31164-27-9

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Nitro-1H-indazole, 97% is used as an intermediate in the synthesis of pharmaceuticals for its versatile chemical properties. It plays a crucial role in the development of new drugs and medications, contributing to advancements in healthcare and medicine.
Used in Agrochemical Production:
In the agrochemical industry, 3-Nitro-1H-indazole, 97% is utilized as a key component in the production of various agrochemicals. Its chemical properties make it suitable for the development of pesticides, herbicides, and other agricultural chemicals, helping to improve crop protection and yield.
Used in Dye Manufacturing:
3-Nitro-1H-indazole, 97% is employed as a raw material in the manufacturing of dyes due to its chemical structure and properties. It contributes to the creation of a wide range of dyes used in various industries, including textiles, plastics, and printing inks, enhancing color vibrancy and performance.
Used in Research and Development:
3-Nitro-1H-indazole, 97% is a valuable compound for research and development purposes. Its high purity and versatile nature make it an ideal candidate for scientific studies and experiments, driving innovation and discovery in various fields, including chemistry, biology, and materials science.

Upstream product

• 271-44-3 benzimidazole 
• 217975-00-3 2-azidobenzyl iodide 
• 95-53-4 o-toluidine 

Downstream Products

• 185011-16-9 1-amino-3-nitroindazole 
• 185011-20-5 1-benzylideneamino-3-nitroindazole 

Relevant academic research and scientific papers

Regioselective N-alkylation of the 1H-indazole scaffold; ring substituent and N-alkylating reagent effects on regioisomeric distribution

The indazole scaffold represents a promising pharmacophore, commonly incorporated in a variety of therapeutic drugs. Although indazole-containing drugs are frequently marketed as the corresponding N-alkyl 1H- or 2H-indazole derivative, the efficient synthesis and isolation of the desired N-1 or N-2 alkylindazole regioisomer can often be challenging and adversely affect product yield. Thus, as part of a broader study focusing on the synthesis of bioactive indazole derivatives, we aimed to develop a regioselective protocol for the synthesis of N-1 alkylindazoles. Initial screening of various conditions revealed that the combination of sodium hydride (NaH) in tetrahydrofuran (THF) (in the presence of an alkyl bromide), represented a promising system for N-1 selective indazole alkylation. For example, among fourteen C-3 substituted indazoles examined, we observed > 99% N-1 regioselectivity for 3-carboxymethyl, 3-tert-butyl, 3-COMe, and 3-carboxamide indazoles. Further extension of this optimized (NaH in THF) protocol to various C-3, -4, -5, -6, and -7 substituted indazoles has highlighted the impact of steric and electronic effects on N-1/N-2 regioisomeric distribution. For example, employing C-7 NO2 or CO2Me substituted indazoles conferred excellent N-2 regioselectivity (≥ 96%). Importantly, we show that this optimized N-alkylation procedure tolerates a wide structural variety of alkylating reagents, including primary alkyl halide and secondary alkyl tosylate electrophiles, while maintaining a high degree of N-1 regioselectivity.

Access to 1: H -indazoles, 1 H -benzoindazoles and 1 H -azaindazoles from (het)aryl azides: A one-pot Staudinger-aza-Wittig reaction leading to N-N bond formation?

The synthesis of various substituted 1H-indazoles is reported through N-N bond formation from an iminophosphorane derivative. Supported by control experiments, an original Staudinger-aza-Wittig tandem mechanism is proposed for this transformation.

Synthesis and some properties of 1-amino-3-nitroindazole

By treating 3-nitroindazole with hydroxylamine-O-sulfonic acid in basic medium, we have obtained its 1-amino derivative. We have observed that in chloroform solution in the presence of triethylamine, it is slowly converted to 1-ethylideneamino-3-nitroinda